2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 86745670、化合物

HRID 1030283ノート

反応式

HRID 1030283 の反応式
[CH2:1]([C:5]1[NH:6][C:7]([C:14]([O:16][CH3:17])=[O:15])=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl>CN(C=O)C.C1COCC1>[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29][N:9]1[C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:6]=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86745670HCID 86745670、化合物収率 106%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

The diester 1 from Step (a) (23 g, MW 240, 0.096 mol) was dissolved in 300 ml DMF. Potassium t-butoxide (100 ml of a 1M solution in dry THF) was added through a syringe. The solution was stirred for 15 min at 25° C. [2-(trimethylsilyl)ethoxy]methyl chloride (SEM-chloride, 18.6 ml, 1.1 eq, MW 166, d 0.94) was added and a precipitate instantly formed. The reaction was stirred for 90 min at 25° C. The solvent was removed and the residue partitioned between ethyl acetate and water. The organic extract was dried over K2CO3 and concentrated. By TLC (SiO2, MeOH-CHCl3 /1-10) a single major spot was observed. This crude product (38 g, 106% yield) was used in subsequent steps without further purification.

後処理

  1. additionwas added
  2. customa precipitate instantly formed
  3. customThe solvent was removed
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionThe organic extract
  6. dry with materialwas dried over K2CO3
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-083931cdec5a451692565c758970fdeb
出典データセット
uspto-grants-1992_04
特許番号
US05104891

反応ノート

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